Formic Acid → HCID 67147726, compound

HRID 506805Notes

Reaction equation

HRID 506805 reaction equation
[CH3:1][O:2][C:3]1N=[C:7]2[C:9]([C:13]3[N:24]([S:25]([C:28]4[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=4)(=[O:27])=[O:26])[C:16]4[N:17]=[CH:18][CH:19]=[C:20]([CH:21]=[N:22]O)[C:15]=4[CH:14]=3)=[CH:10][N:11]([CH3:12])[C:6]2=[CH:5][C:4]=1[O:35][CH3:36].[CH:37](O)=O>C(O)C.O.[Zn]>[O:2]([C:3]1[CH:37]=[C:7]2[C:6](=[CH:5][C:4]=1[O:35][CH3:36])[N:11]([CH3:12])[CH:10]=[C:9]2[C:13]1[N:24]([S:25]([C:28]2[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=2)(=[O:26])=[O:27])[C:16]2=[N:17][CH:18]=[CH:19][C:20]([CH2:21][NH2:22])=[C:15]2[CH:14]=1)[CH3:1]

Participants

6

Reactant 2

HCID 284Formic AcidHCID 1363864872-(5,6-dimethoxy-1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-carbaldehyde oxime

Product 1

HCID 67147726HCID 67147726, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalyst2×HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 0.56 g of [2-(5,6-dimethoxy-1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-carbaldehyde oxime in 30 cm3 of ethanol and 25 cm3 of water, at a temperature in the region of 20° C., is added 0.216 g of zinc and 12 cm3 of concentrated formic acid. A further 0.216 g of zinc is added and the mixture is stirred for a further 24 hours. The reaction medium is stirred at this same temperature for 24 hours. The reaction medium is filtered through Celite and the filtrate is concentrated under reduced pressure. The residue obtained is purified by flash-pack chromatography (SiO2, dichloromethane/methanol 95/05, then dichloromethane/methanol/triethylamine 100/10/1, then dichloromethane/methanol/28% aqueous ammonia 100/10/2 by volume as eluents, Ar). The residue obtained is again purified by flash-pack chromatography (SiO2, dichloromethane/methanol/28% aqueous ammonia 460/40/1.5 by volume as eluents, Ar). 0.03 g of [2-(5,6-dimethoxy1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]methylamine is obtained with the following characteristics:

Workup

  1. stirringThe reaction medium is stirred at this same temperature for 24 hours
  2. filtrationThe reaction medium is filtered through Celite
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. customThe residue obtained
  5. customis purified by flash-pack chromatography (SiO2, dichloromethane/methanol 95/05
  6. customThe residue obtained
  7. customis again purified by flash-pack chromatography (SiO2, dichloromethane/methanol/28% aqueous ammonia 460/40/1.5 by volume as eluents, Ar)

Sources & evidence

ORD record
ord-4148336754c242ebac22504df2382a54
Source dataset
uspto-grants-2010_08
Patent number
US07786114B2

Reaction notes

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